AU681236B2 - Sustained-release dosage forms of alfuzosin hydrochloride - Google Patents

Sustained-release dosage forms of alfuzosin hydrochloride Download PDF

Info

Publication number
AU681236B2
AU681236B2 AU14955/95A AU1495595A AU681236B2 AU 681236 B2 AU681236 B2 AU 681236B2 AU 14955/95 A AU14955/95 A AU 14955/95A AU 1495595 A AU1495595 A AU 1495595A AU 681236 B2 AU681236 B2 AU 681236B2
Authority
AU
Australia
Prior art keywords
composition according
pharmaceutical composition
core
alfuzosin hydrochloride
hydrochloride
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
AU14955/95A
Other versions
AU1495595A (en
Inventor
Veronique Andrieu
Jean Montel
Alexander Wick
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Sanofi Aventis France
Original Assignee
Synthelabo SA
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Synthelabo SA filed Critical Synthelabo SA
Publication of AU1495595A publication Critical patent/AU1495595A/en
Application granted granted Critical
Publication of AU681236B2 publication Critical patent/AU681236B2/en
Assigned to SANOFI-SYNTHELABO reassignment SANOFI-SYNTHELABO Request to Amend Deed and Register Assignors: SYNTHELABO
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
    • A61K31/517—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with carbocyclic ring systems, e.g. quinazoline, perimidine
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/20—Pills, tablets, discs, rods
    • A61K9/28—Dragees; Coated pills or tablets, e.g. with film or compression coating
    • A61K9/2806—Coating materials
    • A61K9/2833—Organic macromolecular compounds
    • A61K9/284—Organic macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyvinyl pyrrolidone
    • A61K9/2846—Poly(meth)acrylates
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/20—Pills, tablets, discs, rods
    • A61K9/28—Dragees; Coated pills or tablets, e.g. with film or compression coating
    • A61K9/2806—Coating materials
    • A61K9/2833—Organic macromolecular compounds
    • A61K9/286—Polysaccharides, e.g. gums; Cyclodextrin
    • A61K9/2866—Cellulose; Cellulose derivatives, e.g. hydroxypropyl methylcellulose
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
    • A61K9/4816—Wall or shell material
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
    • A61K9/50—Microcapsules having a gas, liquid or semi-solid filling; Solid microparticles or pellets surrounded by a distinct coating layer, e.g. coated microspheres, coated drug crystals
    • A61K9/5005—Wall or coating material
    • A61K9/5021—Organic macromolecular compounds
    • A61K9/5026—Organic macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyvinyl pyrrolidone, poly(meth)acrylates
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
    • A61K9/50—Microcapsules having a gas, liquid or semi-solid filling; Solid microparticles or pellets surrounded by a distinct coating layer, e.g. coated microspheres, coated drug crystals
    • A61K9/5005—Wall or coating material
    • A61K9/5021—Organic macromolecular compounds
    • A61K9/5036—Polysaccharides, e.g. gums, alginate; Cyclodextrin
    • A61K9/5042—Cellulose; Cellulose derivatives, e.g. phthalate or acetate succinate esters of hydroxypropyl methylcellulose
    • A61K9/5047—Cellulose ethers containing no ester groups, e.g. hydroxypropyl methylcellulose
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P13/00—Drugs for disorders of the urinary system
    • A61P13/02—Drugs for disorders of the urinary system of urine or of the urinary tract, e.g. urine acidifiers
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P15/00—Drugs for genital or sexual disorders; Contraceptives

Landscapes

  • Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Epidemiology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Urology & Nephrology (AREA)
  • Endocrinology (AREA)
  • Reproductive Health (AREA)
  • Medicinal Preparation (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Polysaccharides And Polysaccharide Derivatives (AREA)
  • Cephalosporin Compounds (AREA)
  • Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)

Abstract

A pharmaceutical prepn. form for targeted release of alfuzosine chlorohydrate is new. The prepn. form comprises a core contg. the active ingredient surrounded by a coating contg. a pH-dependently-soluble polymer.

Description

AUSTRALIA
PATENTS ACT 1990 COMPLETE SPECIFICATION NAME OF APPLICANT(S): Synthelabo ADDRESS FOR SERVICE: DAVIES COLLISON CAVE Patent Attorneys 1 Little Collins Street, Melbourne, 3000.
INVENTION TITLE: Sustained-release dosage forms of alfuzosin hydrochloride The following statement is a full description of this invention, including the best method of performing it known to me/us:- C.
C.
C C CC@
C..
C C o i The present invention relates to targetedrelease pharmaceuticpl forms of alfuzosin hydrochloride and to their application to the preparation of sustained-release dosage forms which are usable for a once-daily administration.
Alfuzosin hydrochloride, used orally in the symptomatic treatment of benign prostatic hypertrophy, displays an absorption whose intensity decreases along the digestive tract, absorption being low in the ileum and colon.
According to a traditional oral form, this compound must hence be administered several times daily.
For alfuzosin hydrochloride, a sustainedrelease oral form enabling a constant plasma concentration which is sufficient over 24 hours to be obtained must effect its release and its absorption mainly in the lower portions of the digestive tract.
The new dosage forms according to the present invention enable the release of alfuzosin hydrochloride ia the digestive tract to be targeted, and are applicable to a once-daily oral administration while being very safe as regards any excessively rapid release.
25 The pharmaceutical forms (compositions) according to the invention contain a core, namely a tablet affording immediate release or sustained release or microparticles affording immediate release of _~s 2 alfuzosin hydrochloride, coated with a membrane whose nature and thickness enable the release of the active principle to be controlled on the basis of pH and time.
The tablets affording immediate or sustained release of the active principle, all the dimensions of which are less than 10 mm, contain 3 to 10 by weight of alfuzosin hydrochloride.
The first kind of tablet is prepared by aqueous granulation from the active principle and excipients such as lactose, microcrystalline cellulose, polyvinylpyrrolidone, sodium carboxymethylstarch and magnesium stearate, the second kind is prepared by aqueous granulation or melting, by combining the active 15 principle with a lipid matrix composed, for example, of microcrystalline cellulose, dicalcium phosphate dihydrate, hydrogenated castor oil, polyvinylpyrrolidone and magnesium stearate.
The microparticles affording immediate 20 release of the active principle contain 3 to 15 by weight of alfuzosin hydrochloride and are between 0.50 and 0* 1.25 mm in size. They are generally prepared by aqueous granulation from the active principle, mannito and S".i polyvinylpyrrolidone.
The tablets and the microparticles are then surrounded by a coating film by spraying with a coating solution in an air-fluidized bed apparatus or any other satisfactory device.
I, LIE I The coating contains a polymer whose dissolution is pH-dependent, for example Eduragit S® (..:ethacrylic acid copolymer) which enables a coating film that dissolves at a pH above 7 to be obtained, thereby effecting a colonic release of the active principle.
The thickness of the coating film enables the latency time of release of the active principle at pH 7 to be modulated.
In the case of microparticles, the coating may further contain an impermeable polymer, and be composed, for example, of a combination of Eudragit S® and ethylcellulose, enabling the rate of release of the active principle to be modulated and effecting, as in the above case, a release of the active principle which is pH- and time-dependent as a result of the presence of the polymer which is soluble at a certain pH and of the thickness of the coating film.
The pharmaceutical forms according to the invention typically contains from 3 to 20 mg of alfuzosin hydrochloride.
They may be used for the preparation of sustained-release dosage forms of alfuzosin 25 hydrochloride for a single daily administration.
These dosage forms can contain one or more pharmaceutical forms having coated cores as are defined above, and, possibly, one or more other pharmaceutical forms having coated or uncoated cores.
L-
Mixing of these different forms enables the release of the active principle to be modulated over the whole length of the digestive tract.
The examples which follow illustrate the invention: ExaMple 1: tablets for colonic targeting.
tablets alfuzosin hydrochloride lactose microcrystalline j~ellulose polyvinylpyrrol idone sodium carboxymethylstarch magnesium stearate 15 coatinq methacrylic acid copolymer diacetylated monoglycerides talc (by weigjht) 3.3 69.4 17.8 9 9t* 9 9..
9 9 999 9 #9*9 9.
99 9 9 99e9 909990 9 0 9. 9 75.7 16.8 ExaMple 2: microparticles for colonic targeting.
0~ 99 9 9 0 990* 90 9 9.
09 microparticles alfuzosin hydrochloride mannitol microcrystalline cellulose polyvinylpyrrol idone %(by weight) 32.0 56.0 coatingr methacrylic acid copolymer ethylcellulose diacetylated monoglycerides 65.0 35.0 Example 3: tablets in a hard gelatin capsule for a once-daily oral administration.
S..9 0. 1.
tablet no. 1 alfuzosin hydrochloride miLcrocrystalline cellulose dicalcium phosphate dihydrate hydrogenated castor oil po lyvinylpyrrol idone magnesium stearate (by weight) 3.3 30.0 42.7 18.0 tablet no. 2 IS alfuzosin hydrochloride lactose microcrystalline cellulose polyvinylpyrrol idon~e sodium carboxymethylstarch 20 magnesium stearate coating~ of the tablet no. 2 methacrylic acid copolymer diacetylated monoglycerides talc 3.3 69.4 17.8 75.7 16.8 6 Tests of dissolution of these different pharnid-autical forms were carried out at pH 2 and at pH 7. The following results were obtained: Formulation according to Example 1, the coating representing 11 of the weight of the tablet and having a thickness of 100 Jm.
dissolved time 0.5 1.0 2.0 pH 2 0 0 0 0 pH 7 0 0 30 100 This formulation, for which the release of alfuzosin hydrochloride is zero at acid pH and complete in the space of 3 hours at pH 7, with a latency time of 1 hour, enables release of the active principle to be effected in the colon.
15 By varying the thickness of the coating film, it is possible to modulate the latency time of release of the active principle at pH 7.
.e.
.:o 9** 9 9 I rY IF L Formulation according to Example 2, the coating representing 14 of the weight of the microparticles.
dissolved time 0.5 1 2 3 4 6 8 pH 2 0.6 2 7 12 17 26 pH 7 1 5 23 47 64 83 91 This formulation, for which the release of alfuzosin hydrochloride varies with the pH, makes it possible to effect a rate of release of the active principle which varies over the whole length of the 10 digestive tract.
Formulation according to Example 3, the coating of the tablet no. 2 representing 11 of the weight of this tablet.
0
S
a.
a a Oa ea a 00 0 *000 dissolved *a a S. a a time 0.5 1 2 3 4 6 8 pH 2 4 8 13 17 19 22 24 pH 7 0.4 4 11 64 89 94 98 This formulation, which combines two types of tablet in the same hard gelatin capsule, effects a release of alfuzosin hydrochloride which is variable with the pH, and hence a rate of release of the active I ~L II principle which is variable over the whole length of the digestive tract.
By increasing the number of tablets affording colonic targeting in the hard gelatin capsule, the amount of active principle released in the colon is increased.
The plasma kinetics of pharmaceutical forms according to the invention were also studied.
The plasma kinetics of tablets affording colonic targeting according to the formulation of Example 1 were determined in twelve healthy volunteers after a single oral administration.
The results obtained showed that the tablet of alfuzosin hydrochloride arrives in the colon after 15 5 hours on average, and that the active principle is
C.
released in a maximum time of 11 hours. The apparent half-life of this formulation is 9 hours.
Moreover, the plasma kinetics of hard gelatin capsules containing tablets of alfuzosin hydrochloride 20 according to the formulation of Example 3 were studied.
The results obtained with three types of capsule containing different proportions of the two types of tablet are shown in Figure 1.
The curve represented by represents the plasma kinetics of a hard gelatin capsule containing 1 uncoated no. 1 tablet containing 3 mg of alfuzosin hydrochloride and 3 coated no. 2 tablets each containing 3 mg of alfuzosin hydrochloride.
L The curve represented by represents the plasma kinetics of a hard gelatin capsule containing 1 uncoated no. 1 tablet containing 5 mg of alfuzosin hydrochloride and 2 coated no. 2 tablets having a dosage identical to that of the no. 2 tablets of the preceding case.
The curve represented by represents the plasma kinetics of a hard gelatin capsule containing 1 unc ed no. 1 tablet containing 3 mg of alfuzosin 10 hydrochloride and 2 coated no. 2 tablets having a dosage identical to that of the no. 2 tablets of the preceding cases.
The results show that this formulation, which enables the release of alfuzosin hydrochloride to be 0 15 modulated over the entire length of the digestive tract, and thus the plasma kinetics to be modified, is suitable for a once-daily administration while being, as a result of the combination of dependency on time S and on pH, very safe for avoiding any more rapid 20 release.
V
9. a.-~-css 4~__CC

Claims (9)

1. Pharmaceutical composition which comprises a core comprising alfuzosin hydrochloride, which core is coated with a coating containing a polymer whose dissolution is pH-dependent.
2. Pharmaceutical composition according to Claim 1, in which the polymer is a methacrylic acid copolymer.
3. Pharmaceutical composition according to Claim 1 or 2, in which the core is a tablet comprising alfuzosin hydrochloride and excipients.
4. Pharmaceutical composition according to Claim 3, in which the core is a tablet consisting of a matrix comprising alfuzosin hydrochloride. Pharmaceutical composition according to Claim 1 or 2, in which the core consists of microparticles.
6. Pharmaceutical composition according to Claim 5, in which the coating further comprises ethylcellulose.
7. Pharmaceutical composition according to any S one of Claims 1 to 6, which comprises from 3 to 20 mg of alfuzosin hydrochloride. S*
8. Pharmaceutical composition according to Claim 1 substantially as hereinbefore described in Example 1 or *9 2 2. .o. Dosage composition which comprises one or more coated cores, as defined in any one of Claims I to 8, and possibly, one or more other coated or uncoated cores comprising a".fuzosin hydrochloride. Dosage composition according to Claim 9, in which the cores -,re contained in a hard gelatin capsule. Dosage composition according to Claim substantially as hereinbefore described in Example 3.
12. A method for the treatment of the human or animal body comprising administering a pharmaceutical composition as defined in any one of Claims 1 to 8 or a dosage composition as defined in Claim 9, 10 or 11.
13. The steps, features, c=positionze and compounds disclosed herein or referred to or indicated in the specification and/or claims of tr,- application, too individually or collectively, and any and all combinations of any t-o or more of said steps or features. "sees. 9:00 0000 DATED this TWENTIETH day of MARCH 1995 Synt! elabo sees by DAVIES COLLISON CAVE 0 a Patent Attorneys for the applicant(s) M I I Abstract Sustained-release compositions of alfuzosin hydrochloride. Pharmaceutical compositions which comprises a core comprising alfuzoain hydrochloride, which core is coated with a coating whose dissolution is pH-dependent and applications to the preparation of sustained- release dosage compositions which are usable for a once-daily oral administration. 9 9.9 o r- II 4qL
AU14955/95A 1994-03-21 1995-03-20 Sustained-release dosage forms of alfuzosin hydrochloride Ceased AU681236B2 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
FR9403257 1994-03-21
FR9403257A FR2717388B1 (en) 1994-03-21 1994-03-21 Extended release dosage forms of alfuzosin hydrochloride.

Publications (2)

Publication Number Publication Date
AU1495595A AU1495595A (en) 1995-09-28
AU681236B2 true AU681236B2 (en) 1997-08-21

Family

ID=9461234

Family Applications (1)

Application Number Title Priority Date Filing Date
AU14955/95A Ceased AU681236B2 (en) 1994-03-21 1995-03-20 Sustained-release dosage forms of alfuzosin hydrochloride

Country Status (19)

Country Link
US (1) US5589190A (en)
EP (1) EP0673650B1 (en)
JP (1) JPH07258085A (en)
KR (1) KR950031052A (en)
CN (1) CN1116524A (en)
AT (1) ATE203672T1 (en)
AU (1) AU681236B2 (en)
CA (1) CA2144917A1 (en)
CZ (1) CZ70495A3 (en)
DE (1) DE69521924T2 (en)
FI (1) FI951300A (en)
FR (1) FR2717388B1 (en)
HU (1) HUT72635A (en)
IL (1) IL113053A (en)
NO (1) NO307813B1 (en)
NZ (1) NZ270748A (en)
PL (1) PL307773A1 (en)
SK (1) SK36595A3 (en)
ZA (1) ZA952290B (en)

Families Citing this family (20)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
IL120302A0 (en) * 1996-03-27 1997-06-10 Pfizer Use of alpha1-adrenoreceptor antagonists in the prevention and treatment of benign prostatic hyperplasia
US6177430B1 (en) 1997-03-27 2001-01-23 Pfizer Inc Use of α1-adrenoreceptor antagonists in the prevention and treatment of benign prostatic hyperplasia
FR2752737B1 (en) * 1996-08-29 1998-10-02 Synthelabo CONTROLLED RELEASE TABLET OF ALFUZOSINE HYDROCHLORIDE
NZ334018A (en) * 1996-08-29 1999-06-29 Synthelabo Multilayered controlled release tablet comprising a layer of alfuzosin hydrochloride and at least one layer of hydrophillic polymers
US20040258750A1 (en) * 1999-06-28 2004-12-23 Gerard Alaux Timed dual release dosage forms comprising a short acting hypnotic or a salt thereof
EP1064938A1 (en) * 1999-06-28 2001-01-03 Sanofi-Synthelabo Pharmaceutical dosage forms for controlled release producing at least a timed pulse
US20020054903A1 (en) * 1999-10-19 2002-05-09 Joseph Tyler Direct compression polymer tablet core
US20060147530A1 (en) * 2002-10-22 2006-07-06 Viswanathan Narayanan B Sustained release compositions containing alfuzosin
CN100372538C (en) * 2004-08-30 2008-03-05 鲁南制药集团股份有限公司 Dispersible tablet of alfuzosin hydrochloride
US20060062846A1 (en) * 2004-09-17 2006-03-23 Cimex Pharma Ag Alfuzosin tablets and synthesis
US20060062845A1 (en) * 2004-09-17 2006-03-23 Cimex Pharma Ag Alfuzosin tablets and synthesis
KR20070021806A (en) * 2005-08-19 2007-02-23 (주)아모레퍼시픽 Sustained-release pellet formulation of ?1-receptor antagonist and process for the preparation thereof
US8206742B2 (en) * 2006-01-12 2012-06-26 Wockhardt Ltd. Sustained release compositions of alfuzosin
US20070292505A1 (en) * 2006-06-15 2007-12-20 Abrika Pharmaceuticals, Inc. Controlled release alfuzosin hydrochloride formulation
US20080095844A1 (en) * 2006-10-23 2008-04-24 Rajhans Sujay Kamalakar Sustained release pharmaceutical compositions of alfuzosin and process for preparation thereof
US20080138412A1 (en) * 2006-12-06 2008-06-12 Fu-Yung Lin Sustained release alfuzosin hydrochl formulation and method for their production
US20100092556A1 (en) * 2006-12-11 2010-04-15 Kristin Arnold Alfuzosin formulations, methods of making, and methods of use
WO2008102235A1 (en) * 2007-02-20 2008-08-28 Aurobindo Pharma Limited Controlled release formulations of alfuzosin
US20100183717A1 (en) * 2009-01-16 2010-07-22 Kristin Arnold Controlled-release formulations
US20120065221A1 (en) 2009-02-26 2012-03-15 Theraquest Biosciences, Inc. Extended Release Oral Pharmaceutical Compositions of 3-Hydroxy-N-Methylmorphinan and Method of Use

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4315007A (en) * 1978-02-06 1982-02-09 Synthelabo 4-Amino-6,7-dimethoxyquinazol-2-yl alkylenediamines
EP0204597A2 (en) * 1985-05-28 1986-12-10 Synthelabo Use of alfuzosine in the treatment of urinary affections

Family Cites Families (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
IE59287B1 (en) * 1984-02-10 1994-02-09 Benzon Pharma As Diffusion coated multiple-units dosage form
DK62184D0 (en) * 1984-02-10 1984-02-10 Benzon As Alfred DIFFUSION COATED POLYDEPOT PREPARATION
US4925837A (en) * 1984-09-14 1990-05-15 Synthelabo Pharmaceutical compositions
US5472710A (en) * 1988-04-16 1995-12-05 Schwarz Pharma Ag Pharmaceutical preparation to be administered orally with controlled release of active substance and method for its manufacture
US5268182A (en) * 1988-06-24 1993-12-07 Abbott Laboratories Sustained-release drug dosage units of terazosin
US5169642A (en) * 1988-06-24 1992-12-08 Abbott Laboratories Sustained-release drug dosage units
US5202128A (en) * 1989-01-06 1993-04-13 F. H. Faulding & Co. Limited Sustained release pharmaceutical composition
US5330766A (en) * 1989-01-06 1994-07-19 F. H. Faulding & Co. Limited Sustained release pharmaceutical composition
US5229131A (en) * 1990-02-05 1993-07-20 University Of Michigan Pulsatile drug delivery system
US5175003A (en) * 1990-04-06 1992-12-29 Biosytes Usa, Inc. Dual mechanism controlled release system for drug dosage forms
AU8050791A (en) * 1990-06-20 1992-01-07 Advanced Polymer Systems Inc. Compositions and methods for the controlled release of soluble active substances
IE61651B1 (en) * 1990-07-04 1994-11-16 Zambon Spa Programmed release oral solid pharmaceutical dosage form
US5316772A (en) * 1990-12-19 1994-05-31 Solvay & Cie, S.A. (Societe Anonyme) Bilayered oral pharmaceutical composition with pH dependent release

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4315007A (en) * 1978-02-06 1982-02-09 Synthelabo 4-Amino-6,7-dimethoxyquinazol-2-yl alkylenediamines
EP0204597A2 (en) * 1985-05-28 1986-12-10 Synthelabo Use of alfuzosine in the treatment of urinary affections

Also Published As

Publication number Publication date
CN1116524A (en) 1996-02-14
NO307813B1 (en) 2000-06-05
PL307773A1 (en) 1995-10-02
NZ270748A (en) 1995-12-21
FI951300A0 (en) 1995-03-20
EP0673650B1 (en) 2001-08-01
DE69521924D1 (en) 2001-09-06
FR2717388A1 (en) 1995-09-22
SK36595A3 (en) 1995-11-08
ZA952290B (en) 1996-01-24
NO951055D0 (en) 1995-03-20
ATE203672T1 (en) 2001-08-15
EP0673650A1 (en) 1995-09-27
HU9500818D0 (en) 1995-05-29
NO951055L (en) 1995-09-22
JPH07258085A (en) 1995-10-09
IL113053A (en) 1999-12-22
KR950031052A (en) 1995-12-18
FR2717388B1 (en) 1996-11-22
FI951300A (en) 1995-09-22
DE69521924T2 (en) 2002-04-11
HUT72635A (en) 1996-05-28
CA2144917A1 (en) 1995-09-22
AU1495595A (en) 1995-09-28
US5589190A (en) 1996-12-31
CZ70495A3 (en) 1995-10-18
IL113053A0 (en) 1995-06-29

Similar Documents

Publication Publication Date Title
AU681236B2 (en) Sustained-release dosage forms of alfuzosin hydrochloride
US5019398A (en) Pharmaceutical composition providing the sustained-release of valproic acid
FI78835B (en) FOERFARANDE FOER FRAMSTAELLNING AV EN NY DIPYRIDAMOL-RETARDFORM.
ES2606463T3 (en) Combination of levodopa / carbidopa immediate release and controlled release dosage forms
US9937132B2 (en) Formulation of doxylamine and pyridoxine and/or metabolites or salts thereof
DK1909766T3 (en) PHARMACEUTICAL FORMULATIONS / FORMATIONS OF guanfacine SUITABLE FOR DAILY ADMINISTRATION IN SINGLE DOSE FORM
RU2325163C2 (en) Lamotrigine-based compositions of prolonged release
KR20080033354A (en) Extended release solid pharmaceutical composition containing carbidopa and levodopa
JP2002527475A (en) Fumaric acid micro tablets
JP2000507613A (en) DFMO containing sustained release formulation
WO2009110005A2 (en) Modified release pharmaceutical compositions comprising mycophenolate and processes thereof
US20070298098A1 (en) Controlled Release Compositions Comprising Levetiracetam
CA2581775A1 (en) Dihydropyrimidine microcapsule - formulations
US20080226738A1 (en) Sustained-Released Pellet Formulation of Alpha1-Receptor Antagonist and Process For the Preparation Thereof
JPS63139128A (en) L-dopa-containing composition, coating method and therapy for parkinsonism
US20090291137A1 (en) Solid oral form provided with a double release profile
WO2006088864A1 (en) Controlled release compositions comprising levetiracetam
JPH0157090B2 (en)
PL192648B1 (en) Pharmaceutical with controlled releose containing inhibitor ace as an active substance
JP4660192B2 (en) Spheroid, method for producing the same, and pharmaceutical composition
US20090155358A1 (en) Pharmaceutical compositions of short-acting hypnotic agents in modified-release forms and the procedures to prepare the mentioned formulation
EP0094123A2 (en) Therapeutic granules
EP1539113A2 (en) Modified release ketoprofen dosage form
JP2016539171A (en) Sustained release pharmaceutical composition comprising acebrofilin and hydrophobic sustained release base
NZ207768A (en) Sustained release tablets comprising dipyridamole

Legal Events

Date Code Title Description
HB Alteration of name in register

Owner name: SANOFI-SYNTHELABO

Free format text: FORMER NAME WAS: SYNTHELABO

MK14 Patent ceased section 143(a) (annual fees not paid) or expired